Toluene → 1-(3-Bromophenyl)-3-(4-fluorophenoxy)azetidine

HRID 522931노트

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HRID 522931 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[F:9][C:10]1[CH:20]=[CH:19][C:13]([O:14][CH:15]2[CH2:18][NH:17][CH2:16]2)=[CH:12][CH:11]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:8][C:4]1[CH:3]=[C:2]([N:17]2[CH2:18][CH:15]([O:14][C:13]3[CH:12]=[CH:11][C:10]([F:9])=[CH:20][CH:19]=3)[CH2:16]2)[CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 5

HCID 1140TolueneHCID 79271,3-DibromobenzeneHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 214287303-(4-Fluorophenoxy)azetidine

생성물 1

HCID 673548151-(3-Bromophenyl)-3-(4-fluorophenoxy)azetidine수율 30%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
100 °C

실험 절차

To a solution of 1, 3-dibromobenzene (500 mg, 2.13 mmol) and 3-(4-fluorophenoxy)azetidine (357 mg, 2.13 mmol) in toluene (7 mL, 3 mmol) was added cesium carbonate (600 mg, 5.3 mmol) and degassed for 15 min. Pd2(dba)3 (97 mg, 0.106 mmol) and BINAP (66 mg, 0.106 mmol) were added and the mixture was heated in the microwave for 30 min at 100° C. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×30 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 1-(3-bromophenyl)-3-(4-fluorophenoxy)azetidine (200 mg, 30%) as a solid. Observed mass (M+1): 322.1.

후처리

  1. customdegassed for 15 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with EtOAc (2×30 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8885093045b5433bb7d6a5a19411150c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334269B2

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